
==== Front
IUCrdata
IUCrdata
IUCrData
IUCrData
2414-3146
International Union of Crystallography

hb4481
10.1107/S2414314624007879
IUCRBK
S2414314624007879
Data Reports
Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-yl­idene]­hydrazinecarbodi­thio­ate
C10H8BrN3OS2
https://orcid.org/0000-0001-9992-0306
Abdul Manan Mohd Abdul Fatah a*
https://orcid.org/0000-0002-5366-9168
Cordes David B. b
https://orcid.org/0000-0002-8578-7054
McKay Aidan P. b
a Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
b EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, United Kingdom
Harrison W. T. A. Editor
University of Aberdeen, United Kingdom
Correspondence e-mail: abdfatah@uitm.edu.my
8 2024
16 8 2024
16 8 2024
9 Pt 8 x240800 x24078705 8 2024
09 8 2024
© Abdul Manan et al. 2024
2024
https://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A full version of this article is available from Crystallography Journals Online.
The crystal structure of a new S-methyl-substituted di­thio­carbazate imine containing the 5-bromo­isatin moiety is described.

The title compound, C10H8BrN3OS2, a brominated di­thio­carbazate imine deriv­ative, was obtained from the condensation reaction of S-methyl­dithio­carbazate (SMDTC) and 5-bromo­isatin. The essentially planar mol­ecule exhibits a Z configuration, with the di­thio­carbazate and 5-bromo­isatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intra­molecular N—H⋯Ob (b = bromo­isatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers characterized by an R22(8) loop motif. In the extended structure, mol­ecules are linked into a three-dimensional network by C—H⋯S and C—H⋯Br hydrogen bonds, C—Br⋯S halogen bonds and aromatic π–π stacking.

crystal structure
di­thio­carbazate
5-bromo­isatin
Z configuration
hydrogen bonding
halogen bond
==== Body
pmcStructure description

Isatin-derived di­thio­carbazate imines have been reported to exhibit a broad spectrum of physiological properties (Yekke-ghasemi et al., 2020 ▸; Ramilo-Gomes et al., 2021 ▸). In particular, the S-methyl-substituted derivatives have received considerable attention in the field of organic transformations for the preparation of carbo­thio­hydrazones, carbo­thio­hydrazides and various aza-heterocyclic compounds such as pyrazoles, 1,2,4-triazoles and 1,3,4-thia­diazo­les (Lin et al., 2013 ▸; Moustafa et al., 2021 ▸; Bekircan et al., 2022 ▸; Malakar et al., 2023 ▸, Geoghegan et al., 2024 ▸). Recent study has revealed that the imine obtained from the condensation reaction of isatin and S-methyl­dithio­carbazate can be directly transformed into the spiro-fused 1,3,4-thia­diazole compound in a straightforward synthetic protocol (Moustafa et al., 2021 ▸). This approach opens a new avenue in accessing isatin-based spiro­cycle mol­ecules. We are concerned with developing new di­thio­carbazate imines containing isatin derivatives and continue research work to explore their potential applications (Abdul Manan et al., 2024 ▸). Therefore, as part of our ongoing research and structural studies on such mol­ecules, we now report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound, C10H8BrN3OS2 contains one mol­ecule and crystallizes in the P21/n monoclinic space group with the S-methyl and thione groups being syn (Fig. 1 ▸). The non-hydrogen atoms in the mol­ecule are close to planar, indicating electron delocalization within the mol­ecule: the dihedral angle between the di­thio­carbazate group and the 5-bromo­isatin ring is 7.9 (3)°. The imine exists in its thione tautomeric form with the di­thio­carbazate unit adopting a Z conformation about the C=N bond [C4—C3=N3—N4 = 177.9 (9)°] with respect to the 5-bromo­isatin moiety, while the S10 thio­keto sulfur atom is positioned anti to the N3 azomethine nitro­gen atom [N3—N4—C10—S10 = 173.8 (7)°]. The presence of an N—H⋯Ob (b = bromo­isatin) intra­molecular hydrogen helps to consolidate the planar conformatic of the title mol­ecule (Table 1 ▸). Otherwise, the bond lengths and angles are comparable to those reported for methyl 2-(5-chloro-2-oxo-1,2-di­hydro-3H-indol-3-yl­idene)hydrazine­carbodi­thio­ate (Abdul Manan et al., 2011 ▸), methyl 2-(1-methyl-2-oxo-1,2-di­hydro-3H-indol-3-yl­idene)hydrazine­carbodi­thio­ate (Abdul Manan et al., 2012 ▸) and methyl (Z)-2-(5-fluoro-2-oxo-1,2-di­hydro-3H-indol-3-yl­idene)hydrazine-1-carbodi­thio­ate (Li et al., 2018 ▸).

In the crystal of the title compound, mol­ecules are linked into dimers through pairwise N1—H1⋯O2 hydrogen bonds in a common (8) motif (Fig. 2 ▸). These dimers further pack into chains propagating along [20] through a combination of weak C5—H5⋯Br5 hydrogen bonds and Br5⋯S11 [Br⋯S = 3.521 (3) Å, C—S⋯Br = 135.1 (3)°, C—Br⋯S = 155.2 (3)°] halogen bonds, forming a extended (9)(8)(9) motif. These chains are connected into the third dimension by further weak C7—H7⋯S10 hydrogen bonds (Table 1 ▸, Fig. 3 ▸). These hydrogen bonded arrays have parallel mol­ecules separated such that an equivalent inter­penetrating mol­ecular framework exists, inter­acting with the other via aromatic π–π stacking [N1/C2–C4/C9, centroid⋯centroid separation = 3.307 (9) Å].

Synthesis and crystallization

The di­thio­carbazate precursor, SMDTC was prepared by the literature method (Das & Livingstone, 1976 ▸). The title compound was prepared by adding 5-bromo­isatin (2.26 g, 10.0 mmol, 1.0 eq) dissolved in hot ethanol (20 ml) to a solution of the precursor, SMDTC (1.22 g, 10.0 mmol, 1.0 eq) in hot ethanol (35 ml). The mixture was heated (80°C) with continuous stirring for 15 min and later allowed to stand about 20 min at room temperature until a precipitate was formed, which was then filtered and dried over silica gel, yielding orange crystals on recrystallization from ethanol solution (yield: 2.74 g, 83%). m.p. 259–260°C; 1H NMR (400 MHz, d6-DMSO) δ: (p.p.m.): 2.63 (s, 3H), 6.92 (d, J = 8.28 Hz, 1H), 7.59 (dd, J = 8.32, 2.0 Hz, 1H), 7.63 (d, J = 1.92 Hz, 1H), 11.48 (s, 1H), 13.90 (s, 1H); HRMS m/z (ESI+), found: [M + H]+ 329.9335, C10H8N3OS279Br requires [M + H]+ 329.9370.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The structure was refined as a two-component twin with component 2 rotated by −176.99° around [0.92 0.02 − 0.38] (reciprocal) or [1.00 0.02 0.00] (direct), and a refined twin fraction of 0.056 (3).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624007879/hb4481sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624007879/hb4481Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314624007879/hb4481Isup3.cml

CCDC reference: 2376721

Additional supporting information: crystallographic information; 3D view; checkCIF report

The authors acknowledge Universiti Teknologi MARA for financial support.

full crystallographic data

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Crystal data

C10H8BrN3OS2	F(000) = 656	
Mr = 330.22	Dx = 1.782 Mg m−3	
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å	
a = 6.6331 (3) Å	Cell parameters from 3279 reflections	
b = 7.5726 (3) Å	θ = 3.6–75.3°	
c = 24.6985 (10) Å	µ = 7.63 mm−1	
β = 97.141 (4)°	T = 125 K	
V = 1230.98 (9) Å3	Needle, orange	
Z = 4	0.11 × 0.01 × 0.01 × 0.40 (radius) mm	

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Data collection

Rigaku XtaLAB P200K diffractometer	2513 independent reflections	
Radiation source: Rotating Anode, Rigaku MM-007HF	1869 reflections with I > 2σ(I)	
Rigaku Osmic Confocal Optical System monochromator	Rint = 0.193	
Detector resolution: 5.8140 pixels mm-1	θmax = 76.3°, θmin = 6.1°	
shutterless scans	h = −7→7	
Absorption correction: multi-scan (CrysAlisPr; Rigaku OD, 2023)	k = −9→9	
Tmin = 0.025, Tmax = 0.114	l = −5→30	
11959 measured reflections		

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Refinement

Refinement on F2	Primary atom site location: dual	
Least-squares matrix: full	Hydrogen site location: mixed	
R[F2 > 2σ(F2)] = 0.093	H atoms treated by a mixture of independent and constrained refinement	
wR(F2) = 0.293	w = 1/[σ2(Fo2) + (0.145P)2 + 4.1265P] where P = (Fo2 + 2Fc2)/3	
S = 1.14	(Δ/σ)max < 0.001	
2513 reflections	Δρmax = 1.37 e Å−3	
164 parameters	Δρmin = −1.06 e Å−3	
2 restraints		

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.	
Refinement. Refined as a 2-component twin with HKLF5 generated by TWINROTMAT running in PLATON. NH hydrogen atoms were identifed from Fmap and refined with N-H restrained to 0.98 Å.	

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

	x	y	z	Uiso*/Ueq		
Br5	−0.00632 (16)	0.49654 (14)	0.40002 (4)	0.0565 (4)		
S11	0.3366 (4)	0.2379 (4)	0.68815 (10)	0.0606 (7)		
S10	0.7209 (4)	0.0479 (4)	0.73636 (10)	0.0602 (7)		
O2	0.9075 (10)	0.0482 (9)	0.5665 (3)	0.0519 (15)		
N1	0.7784 (13)	0.1254 (11)	0.4779 (3)	0.0497 (17)		
N4	0.6432 (12)	0.1539 (11)	0.6357 (3)	0.0500 (17)		
N3	0.5194 (11)	0.2188 (10)	0.5925 (3)	0.0471 (17)		
C2	0.7769 (15)	0.1156 (13)	0.5335 (4)	0.051 (2)		
C6	0.2344 (13)	0.3758 (12)	0.4224 (4)	0.048 (2)		
C9	0.5992 (16)	0.2052 (13)	0.4534 (4)	0.052 (2)		
C4	0.4781 (16)	0.2581 (12)	0.4928 (4)	0.050 (2)		
C5	0.2935 (15)	0.3440 (12)	0.4784 (4)	0.0483 (19)		
H5	0.210762	0.379717	0.505144	0.058*		
C10	0.5760 (17)	0.1466 (13)	0.6859 (4)	0.054 (2)		
C7	0.3544 (14)	0.3217 (13)	0.3840 (4)	0.051 (2)		
H7	0.309938	0.343966	0.346543	0.061*		
C11	0.3089 (19)	0.2206 (17)	0.7602 (5)	0.065 (3)		
H11A	0.175584	0.266410	0.766485	0.098*		
H11B	0.415852	0.289473	0.781506	0.098*		
H11C	0.320165	0.096497	0.771421	0.098*		
C8	0.5376 (16)	0.2359 (13)	0.3979 (4)	0.053 (2)		
H8	0.618622	0.199134	0.370855	0.064*		
C3	0.5842 (16)	0.2045 (13)	0.5453 (4)	0.052 (2)		
H4	0.753 (10)	0.069 (10)	0.633 (4)	0.04 (2)*		
H1	0.881 (13)	0.046 (12)	0.467 (4)	0.05 (3)*		

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Atomic displacement parameters (Å2)

	U11	U22	U33	U12	U13	U23	
Br5	0.0560 (7)	0.0579 (7)	0.0547 (7)	0.0055 (4)	0.0036 (5)	0.0015 (4)	
S11	0.0661 (15)	0.0663 (15)	0.0499 (13)	0.0133 (12)	0.0089 (11)	0.0043 (11)	
S10	0.0692 (16)	0.0626 (15)	0.0472 (13)	0.0112 (12)	0.0007 (11)	0.0017 (11)	
O2	0.049 (4)	0.055 (4)	0.051 (3)	0.004 (3)	0.002 (3)	−0.001 (3)	
N1	0.060 (5)	0.048 (4)	0.043 (4)	0.000 (3)	0.012 (3)	−0.001 (3)	
N4	0.052 (4)	0.047 (4)	0.050 (4)	0.007 (3)	0.004 (3)	0.002 (3)	
N3	0.049 (4)	0.042 (4)	0.050 (4)	0.002 (3)	0.002 (3)	0.000 (3)	
C2	0.058 (5)	0.047 (5)	0.047 (5)	−0.009 (4)	0.008 (4)	−0.006 (4)	
C6	0.034 (4)	0.046 (4)	0.061 (5)	0.000 (3)	−0.008 (4)	0.001 (4)	
C9	0.060 (6)	0.043 (5)	0.056 (5)	−0.005 (4)	0.013 (4)	−0.001 (4)	
C4	0.067 (6)	0.038 (4)	0.043 (4)	−0.003 (4)	0.002 (4)	−0.003 (3)	
C5	0.058 (5)	0.042 (4)	0.044 (5)	−0.007 (4)	0.002 (4)	−0.002 (3)	
C10	0.074 (6)	0.043 (5)	0.046 (5)	0.004 (4)	0.007 (4)	−0.002 (4)	
C7	0.052 (5)	0.055 (5)	0.046 (5)	−0.002 (4)	0.009 (4)	0.006 (4)	
C11	0.070 (7)	0.070 (7)	0.058 (6)	0.009 (5)	0.019 (5)	−0.004 (5)	
C8	0.060 (6)	0.052 (5)	0.049 (5)	−0.011 (4)	0.013 (4)	0.000 (4)	
C3	0.059 (5)	0.046 (5)	0.052 (5)	−0.001 (4)	0.012 (4)	−0.004 (4)	

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Geometric parameters (Å, º)

Br5—C6	1.863 (8)	C6—C5	1.410 (13)	
S11—C10	1.739 (11)	C6—C7	1.375 (14)	
S11—C11	1.816 (11)	C9—C4	1.395 (14)	
S10—C10	1.654 (10)	C9—C8	1.399 (14)	
O2—C2	1.224 (12)	C4—C5	1.394 (14)	
N1—C2	1.378 (12)	C4—C3	1.455 (13)	
N1—C9	1.402 (13)	C5—H5	0.9500	
N1—H1	0.97 (2)	C7—H7	0.9500	
N4—N3	1.355 (11)	C7—C8	1.383 (15)	
N4—C10	1.371 (13)	C11—H11A	0.9800	
N4—H4	0.98 (2)	C11—H11B	0.9800	
N3—C3	1.294 (12)	C11—H11C	0.9800	
C2—C3	1.505 (14)	C8—H8	0.9500	
				
C10—S11—C11	101.9 (5)	C4—C5—C6	117.3 (9)	
C2—N1—C9	110.1 (8)	C4—C5—H5	121.3	
C2—N1—H1	110 (7)	S10—C10—S11	127.1 (6)	
C9—N1—H1	137 (7)	N4—C10—S11	114.4 (7)	
N3—N4—C10	119.6 (8)	N4—C10—S10	118.4 (8)	
N3—N4—H4	124 (5)	C6—C7—H7	118.9	
C10—N4—H4	111 (5)	C6—C7—C8	122.3 (9)	
C3—N3—N4	116.2 (8)	C8—C7—H7	118.9	
O2—C2—N1	126.5 (9)	S11—C11—H11A	109.5	
O2—C2—C3	127.3 (9)	S11—C11—H11B	109.5	
N1—C2—C3	106.3 (8)	S11—C11—H11C	109.5	
C5—C6—Br5	119.9 (7)	H11A—C11—H11B	109.5	
C7—C6—Br5	119.3 (7)	H11A—C11—H11C	109.5	
C7—C6—C5	120.8 (8)	H11B—C11—H11C	109.5	
C4—C9—N1	110.7 (9)	C9—C8—H8	121.2	
C4—C9—C8	120.8 (10)	C7—C8—C9	117.5 (9)	
C8—C9—N1	128.5 (9)	C7—C8—H8	121.2	
C9—C4—C3	106.6 (9)	N3—C3—C2	126.6 (9)	
C5—C4—C9	121.3 (9)	N3—C3—C4	126.9 (9)	
C5—C4—C3	132.1 (9)	C4—C3—C2	106.3 (8)	
C6—C5—H5	121.3			
				
Br5—C6—C5—C4	−178.0 (7)	C9—N1—C2—O2	177.5 (9)	
Br5—C6—C7—C8	178.1 (8)	C9—N1—C2—C3	−2.8 (10)	
O2—C2—C3—N3	−3.0 (17)	C9—C4—C5—C6	−0.2 (14)	
O2—C2—C3—C4	−178.5 (9)	C9—C4—C3—N3	−175.6 (10)	
N1—C2—C3—N3	177.3 (9)	C9—C4—C3—C2	−0.2 (10)	
N1—C2—C3—C4	1.8 (10)	C4—C9—C8—C7	0.6 (14)	
N1—C9—C4—C5	178.7 (8)	C5—C6—C7—C8	−0.6 (15)	
N1—C9—C4—C3	−1.6 (11)	C5—C4—C3—N3	4.0 (17)	
N1—C9—C8—C7	−178.4 (9)	C5—C4—C3—C2	179.5 (10)	
N4—N3—C3—C2	3.3 (14)	C10—N4—N3—C3	−172.9 (9)	
N4—N3—C3—C4	177.9 (9)	C7—C6—C5—C4	0.7 (13)	
N3—N4—C10—S11	−3.9 (12)	C11—S11—C10—S10	6.9 (9)	
N3—N4—C10—S10	173.8 (7)	C11—S11—C10—N4	−175.7 (8)	
C2—N1—C9—C4	2.9 (11)	C8—C9—C4—C5	−0.5 (14)	
C2—N1—C9—C8	−178.0 (10)	C8—C9—C4—C3	179.2 (9)	
C6—C7—C8—C9	−0.1 (15)	C3—C4—C5—C6	−179.8 (10)	

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A	
N4—H4···O2	0.98 (2)	2.04 (8)	2.715 (11)	124 (7)	
N1—H1···O2i	0.97 (2)	1.86 (4)	2.801 (11)	163 (10)	
C5—H5···Br5ii	0.95	3.00	3.941 (10)	172	
C7—H7···S10iii	0.95	2.83	3.775 (10)	171	

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1/2, −y+1/2, z−1/2.

Figure 1 The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Figure 2 View of the dimers formed by N—H⋯O hydrogen-bonding giving (8) motifs.

Figure 3 View showing both the weak hydrogen bonds and halogen bonds connecting the hydrogen-bonded dimers in three-dimensions.

Table 1 Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A	
N4—H4⋯O2	0.98 (2)	2.04 (8)	2.715 (11)	124 (7)	
N1—H1⋯O2i	0.97 (2)	1.86 (4)	2.801 (11)	163 (10)	
C5—H5⋯Br5ii	0.95	3.00	3.941 (10)	172	
C7—H7⋯S10iii	0.95	2.83	3.775 (10)	171	
Symmetry codes: (i) ; (ii) ; (iii) .

Table 2 Experimental details

Crystal data	
Chemical formula	C10H8BrN3OS2	
M r	330.22	
Crystal system, space group	Monoclinic, P21/n	
Temperature (K)	125	
a, b, c (Å)	6.6331 (3), 7.5726 (3), 24.6985 (10)	
β (°)	97.141 (4)	
V (Å3)	1230.98 (9)	
Z	4	
Radiation type	Cu Kα	
μ (mm−1)	7.63	
Crystal size (mm)	0.11 × 0.01 × 0.01 × 0.40 (radius)	
 	
Data collection	
Diffractometer	Rigaku XtaLAB P200K	
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2023 ▸)	
Tmin, Tmax	0.025, 0.114	
No. of measured, independent and observed [I > 2σ(I)] reflections	11989, 2513, 1869	
R int	0.1931	
(sin θ/λ)max (Å−1)	0.630	
 	
Refinement	
R[F2 > 2σ(F2)], wR(F2), S	0.093, 0.293, 1.14	
No. of reflections	2513	
No. of parameters	164	
No. of restraints	2	
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	
Δρmax, Δρmin (e Å−3)	1.37, −1.06	
Computer programs: CrysAlis PRO (Rigaku OD, 2023 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2019/3 (Sheldrick, 2015b ▸), Mercury (Macrae et al., 2020 ▸), OLEX2 (Dolomanov et al., 2009 ▸) and publCIF (Westrip, 2010 ▸).
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References

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